When Good Habits Become Shackles: A Lesson from John

Here I am, sitting at my kitchen table, coffee in hand, reflecting on a conversation that shifted my perspective on habits—and life itself.

I met John on my flight to Cambodia. A semi-retired gentleman in his mid-70s, John had built a solid life: a long career, strong family ties, and a steady, structured routine.

He spoke with immense pride about his family, though he didn’t mention their names—just their career titles. The lawyer. The teacher. It was clear that success, status, and stability were important to him.

John was heading to Vietnam to meet a group of people, including a man he’d crossed paths with before—a successful entrepreneur who had no roots. John couldn’t quite wrap his head around it.

“How can you live without roots?” he wondered aloud. He was determined to convince this man to settle down.

I listened, sensing the tension between John's deep attachment to stability and his curiosity about the freedom this entrepreneur represented. After some back and forth, he asked me what I did for work.

“I’m a life coach,” I said. And then I stayed silent.

I could tell John was giving it some thought. He asked a few questions about what life coaching involved.

Then he asked, “So what’s the first thing you do when you meet a client?”

"To build a trusting environment with them because it’s the foundation for success in a client/coach relationship," I replied.

Another pause. I could see him weighing his next words carefully.

"I struggle with my mindset," he finally admitted.

And there it was—the opening for the most incredible conversation.

Our conversation spanned the entire six-hour flight. We covered so many topics—life, career, family, mindset—but the part that stayed with me most was John's six-decade span of journaling. 

Journaling as Shackles

John revealed that he’s been journaling every single day since January 1, 1963—when he was nine years old. That’s over 62 years of daily journaling. I was blown away!!

But here’s the part that struck me: John referred to his journaling as “shackles.”

He said it’s something he has to do. I asked if he’d ever missed a day. "No, never." "Would you consider skipping a day?" I asked. "Maybe… but probably not," he said, with a hint of hesitation.

I sensed fear beneath his words—the idea of not journaling, even for one day, felt unsettling to him. And then he shared something that made everything click: his dad had asked him to start journaling all those years ago.

Suddenly, it all made sense. This habit perhaps wasn’t just about self-reflection—perhaps it was rooted in obligation, in pleasing his father. Somewhere along the way, that external expectation became internalised.

Journaling wasn’t just a habit anymore—it was part of his identity. Letting it go, even for a day, might feel like losing a piece of himself.

When Good Habits Become Cages

John’s story made me think: how often do we stick to habits because they genuinely serve us—and how often are we clinging to them out of obligation or fear?

Good habits can quietly become cages when they lose their intentionality. What starts as a conscious choice can harden into a compulsion, driven by the need to feel in control or to meet an unspoken expectation.

John’s journaling began as an act of connection with his father. But over time, it transformed into something he couldn’t imagine letting go of—not because he still wanted to journal, but because he felt he had to.

That’s the fine line between discipline and compulsion.

The Power of Intention

My takeaway from John’s story was profound: even positive habits need to be reevaluated from time to time. The real power lies not in the act itself, but in the intention behind it.

Here’s the question I keep coming back to: "If you stopped doing this habit tomorrow, what would you fear losing?"

That’s the key. If the answer is peace, growth, or clarity—that’s a habit aligned with your true self. But if the answer is fear, guilt, or the sense of losing control—that’s a habit worth re-examining.

John taught me that sometimes, the bravest thing we can do isn’t adding more structure or discipline—it’s letting go of the habits we’ve outgrown.

And maybe—just maybe—John will wake up one morning and choose to skip a day of journaling. Not because he’s lost his way, but because he’s finally found the freedom to choose.

"Have you ever had a habit that started with intention but became more of an obligation over time?

Let me know in the comments—I'd love to hear your thoughts."